Say what you will about Debra Ryan, but the girlfriend of convicted hedge fund fraudster Samuel Israel is unfailingly loyal.

Ryan was arrested Friday and charged with trying to send $300 in cash to the Bayou Group founder. It’s her second arrest for allegedly trying to help her swindler paramour out by less-than-legal means: The introducing contraband into prison charge was disclosed in White Plains federal court today, after Ryan pleaded not guilty to charges she helped Israel skip bail this summer.

Prisoners at the Westchester County jail are not allowed to receive cash.

Westchester County, N.Y., police say the money was “secreted in the pages of a magazine” and was discovered during a routine screening of prisoner mail. The shipment was traced to Ryan, who lives in Armonk, north of New York City. She is due to appear in county court on the charge later this month; she faces as much a year in prison on the contraband charge.

U.S. District Judge Kenneth Karas, who heard her plea on the federal bail-jumping charges, warned her to have “no contact of any kind” with her boyfriend, saying that further infractions could imperil her $75,000 bail.

“Ms. Ryan, please don’t tempt fate,” Karas said at today’s hearing.

Ryan was arrested on June 10, a day after Israel failed to report to the same Massachusetts prison in which he is now undergoing a psychological evaluation to begin a 20-year sentence. Israel’s SUV was found idling on a bridge north of New York City with the words “suicide is painless” scrawled on the hood. Authorities quickly concluded that Israel faked his death,

Ryan reportedly confessed that she helped Israel plan his fake suicide and flight, although she has pleaded not guilty to the bail-jumping charges. According to police, Ryan admitted she helped him pack the recreational vehicle in which Israel went on the run, and helped him drop the RV off at an interstate rest area. He was apparently picked up from the bridge later on June 9 and dropped off at the rest area. Israel surrendered to authorities in Massachusetts on July 2.

Ryan faces up to 10 years in prison on the federal charges of aiding and abetting her boyfriend’s failure to report to prison. But prosecutor Nicholas McQuade told Karas that plea bargain talks are underway, and that the case is unlikely to go to trial. Ryan is due back in court on Feb. 10.

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